by Esther Schindler

The Executive Woman’s Guide to Mentoring

Feb 25, 200812 mins

Successful women who've served in both roles explain what makes a mentoring relationship work, how to find the right person and knowing when to part.

Every stage in your career progress requires new skills. Sometimes, the knowledge you need to acquire is technical minutiae that can best be learned with a more experienced practitioner at your elbow. At other times, you need advice about developing business skills, or help deciding which new position to accept. Such advice can be acquired haphazardly, or it can come from a mentoring relationship.


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However, finding a suitable mentor or mentee and making the relationship work isn’t always easy, particularly for women who are shy about asking for assistance. Executive women in IT who have learned from mentors or who have provided such guidance themselves urge others to get involved, no matter where they are on their career path. In this article, successful women share what makes a mentoring relationship work, how to find the right person and how to know when to part.

The Benefits of Mentoring Go Both Ways

Mentoring is worth the energy expended, both for an executive who offers guidance and for the person who listens. Everyone interviewed for this article who had mentoring relationships (as mentor, mentee or both), speaks warmly of the experience and cites personal and professional abilities gained.

For the mentee, the real value of mentoring comes from the opportunity to gain confidence as well as skills. “It’s a relationship with someone who allows you to voice your vulnerabilities, coach you on strategies to overcome them and help you see possibilities you might have missed otherwise,” says Diane Wallace, CIO of the Connecticut Department of Information Technology.

The career benefits can be significant for the mentor, too. Mandeep Maini, vice president of healthcare systems marketing and web systems delivery at Blue Cross/Blue Shield, says executives should “Mentor to learn, rather than to teach.” Mentoring makes you reflect on your own style, prejudices and shortcomings, she says, and encourages soul searching.

Mentoring has also made Maini a more compassionate and inclusive leader. A mentee from another department was nervous about speaking up in meetings—a difficulty that Maini personally never had. Coaching her mentee through her fears caused Maini to recognize that someone in her own department who doesn’t speak up may be holding back out of shyness, rather than out of a lack of things to say. So Maini is now more inclined to solicit the meeting participant’s opinion, where she wouldn’t have done so previously.

What’s more, mentors say they derive a sense of satisfaction from helping the next generation gain the skills they need. Connecticut’s Wallace counts all the successful managers and leaders she’s mentored who went on to bigger and better assignments as one of her greatest achievements. “I’m still in touch with employees who I haven’t worked with in years, but who still choose to call me a friend because I helped mentor them at some point,” she says.

The benefits are evident no matter where you stand on the job ladder—and it’s particularly valuable for executives, says Maini, since it’s lonely at the top. Executives rarely want to express uncertainty since it makes others think they can’t do the job. Yet, Maini points out, we all have fears and insecurities and need to talk with someone.

Linda Brigance, vice president and CIO of FedEx’s Asia Pacific Division, appreciates someone who can provide guidance. “I had a mentor even as I moved into my role as CIO in Asia, which provided me with the comfort and confidence that I could talk with someone I trusted as I was establishing myself in this role.”

Mentoring Nuts & Bolts

Those who have never sought a mentor may be unsure how it works day-to-day or be unclear about the specifics of such relationships.

The short answer, of course, is that a mentoring relationship can work any way that satisfies the participants. That being said, a typical mentoring relationship consists of an agreement to work together for a period of time, such as six to nine months, with hour-long phone calls or video conferences once a month. Wallace recommends that mentees share their résumé, long-term career development objectives and what they hope to accomplish through the mentoring relationship prior to the first meeting. Wallace also suggests that the mentee itemize current performance objectives that will influence her career and three challenges in her development process. “These documents then become the basis of the first conversation in establishing how the mentor can help the mentee,” says Wallace.

Typical discussion topics include challenges in the mentee’s current job (such as a difficult project or clash with a superior or peer) or a family/work balance issue with which the individual is wrestling. “The point of these conversations is to have a safe place to discuss issues and get a new, unbiased perspective on how to handle them.”

Be prepared, says Wallace, and schedule a conversation when it’s convenient for the mentor. “If you haven’t worked for them before, you want to approach them on an issue of mutual interest. If that initial conversation goes well, ask if you can seek their advice on other issues,” she says. “Mentoring conversations don’t need to take an hour; 10 to 15 minutes can be a lot of time if you’re prepared and can get to the point.”

The result of such conversations is both tactical—better ways to do your job—and strategic. When asked what she got from mentoring, Charlotte Klock, executive director of IT infrastructure at the University of California-San Diego identified several reoccurring themes, such as “pick your battles” and “it’s OK to take risks.” Would she have learned these lessons otherwise? “Probably, but I would have burned a lot of bridges in doing so and created a bunch of work that wasn’t necessary.”

Finding a Mentor or Mentee

It’s common for people to find their mentors from an existing work relationship, such as the boss who continues to offer advice. Others prefer to get their guidance from elsewhere in the organization or from outside the company to avoid departmental politics.

Clearly, both approaches can work, but the important point is to find someone from whom you can learn. “Look to people who embody the characteristics you aspire to develop,” says Maini. Brigance recommends identifying role models: individuals for whom you have the most respect because of their actions and decisions as professionals.

You also want to make sure you can relate to your mentor or mentee. For Suzanne Montague, CIO and vice president for IT at University of Texas at Arlington’s Office of Information Technology, compatibility is most important. “I think there needs to be an alignment of business philosophies,” she says. “This includes an agreement on business priorities, goals, strategies, tactics and beliefs. I have seen many situations where a possible mentoring relationship started to bud, then lost momentum due to a misalignment in one of these critical areas.”

Don’t be shy about asking a would-be mentor if she’d be interested in helping you. Most people are honored to be asked, says Maini; after all, who can resist the flattery of being told she’s a role model?

“The most successful mentor-mentee relationships usually occur when a colleague or associate has reached out to me proactively,” says FedEx’s Brigance. “When this happens, it clearly demonstrates to me that this person is deeply interested in expanding their knowledge, experience and appetite for growth.”

Adds Klock, senior managers always have an opportunity to provide mentoring, even when the recipient isn’t consciously aware of the nature of the guidance. You can show how to conduct meetings, work one-on-one with your staff, or decide how much risk to take.

When you look for someone to mentor or from whom to get mentoring, it’s far more important to concern yourself with a match of skills and interests than with whether the mentor is a man or a woman. You do need to be comfortable with the individual, and maybe that means you’ll lean towards one or the other—but it’s far from the primary criteria.

Women interviewed for this story say gender usually is not an issue. Gender plays no role in a successful mentoring relationship, says Brigance, who adds that she has had excellent male and female mentors and that she has mentored both men and women. “What matters is that both the mentor and mentee have mutual respect for each other.”

Pamela Rucker, vice president of IT at PSC, which provides nationwide industrial services, environmental services, transportation and container services, agrees that a gender match isn’t critical but emphasizes that it be appropriate. “Having a woman who understands what it’s like to be the only female at the table in an executive setting helps you relate on a different level,” she says. “There’s an unspoken camaraderie that comes from a person sharing your same background.”

Creating a Mentoring Relationship

Mentoring can work well whether the relationship is announced (that is, both parties explicitly label their relationship as mentoring) or it’s informal. Those seeking the informal relationships, anecdotally speaking, seem to pick the chain-of-command, such as a manager who takes an interest in a junior staff member’s career and keeps in touch after each moves on. For example, Wallace’s mentees generally are people who work for her, either directly or, more often, lower in the organization.

But mentoring can come from formalized “matchmaking” too. Although she’s had informal mentors and works actively as a volunteer with young women exploring IT, Maini’s primary mentoring experience has been within the confines of Blue Cross/Blue Shield’s formal mentoring program. The company’s program is available for all employees (not just in IT) and to both men and women. Mentors and mentees are matched on résumés and on what the participants identify as areas upon which they want to improve.

Wallace joined Menttium, an organization that matches senior executives with up and coming women managers. “Through Menttium,” she says, “I was paired with a mentee I would never have known otherwise. The Menttium relationship was the most formal because we didn’t have a work environment in common and had to define the things we were going to work on together.”

Making Mentoring Succeed

There are few horror stories about Mentoring Gone Bad. Nevertheless, executive women have plenty of advice about how to get the most from these relationships.

Honest and regular communication is among the most important factors, says Brigance. “It is all about establishing a connection and the mutual respect that enables you and your mentee to feel comfortable enough to ask questions and provide constructive feedback,” she says. In an ideal relationship, she adds, the mentor should understand her mentee’s strengths and weaknesses, just as the mentee should be receptive to hearing unvarnished feedback.

Confidentiality is critical. Mentors and mentees must be careful not to expose the other’s vulnerabilities outside the coaching session. “The mentor must respect this issue if trust is to be established for the most productive mentoring relationships,” says Wallace.

The mentor has the responsibility of bringing unbiased, confidential advice to help her mentee perform more effectively. It’s also key, says Linda Siksna, vice president of IT shared services at Canadian Tire Corporation, to remain objective. To that end, Siksna feels it’s important that the mentor and mentee not report to one another, directly or indirectly in the same organization.

“It’s not enough to expose a person to what you do; you must take time to expose them to who you are,” advises PSC’s Rucker. She recommends describing your career path to the mentee so she can see that the mentor’s accomplishments are also possible for her. “If a mentoring relationship fails, it’s because the mentee never found the personal connection that transforms time spent with you into time becoming you. Somewhere, somehow, they need to see themselves in you and know that what you’ve done, they can do also,” says Rucker.

Finally, mentoring can only work if you commit the time to make it work properly, and you focus on the mentee’s needs, says Wallace. “As a mentor, I like to reach out to people who are promising men and women—those who work hard to deliver results and bring a passion to what they do. I want to help these people make progress in their careers.”

Parting Ways?

When do you know it’s time for the relationship to end—positively or negatively?

Usually, it’s pretty obvious. Brigance recommends that the participants set up an agenda to focus on at the outset of the mentoring relationship. “Depending on how many areas you identify, you can mutually agree on the length of the relationship,” she says.

For Klock, a mentoring relationship should end when both parties feel they have met their objectives, or when they determine that the objectives are no longer important to complete. Formal mentoring also can end when the mentee reaches the point of being more of a peer either inside or outside of the company. This does not mean that the mentee can never again approach her mentor. “I still go back to a few mentors for advice periodically. I don’t know that I have ever shut off that relationship completely,” says Klock.

Indeed, “old” mentoring relationships often turn into friendships. “Those relationships go on forever,” says Maini.

When the relationship isn’t working out, it’s important to be honest. “It’s better to part than to make it burdensome,” says Maini. “Just be adult about it.”

Being a mentor isn’t always easy. Aside from the time and energy requirements, a mentor has to remain neutral in helping a mentee handle a problem. The mentor must leave out her own feelings (i.e. what she would do personally) in coaching the mentee to weigh all options and come to a conclusion herself, says Klock.

Despite mentoring’s challenges, it’s worth the effort to earn the rewards. Says Maini, “Mentoring is important and should play a role in one’s career. Use the experience to grow and navigate and move up.”

The women in this story are all members of the CIO Executive Council, a professional association of IT leaders founded by CIO magazine. The Council runs a networking and best-practice-sharing program for women IT executives. For more information on this program and Council membership, visit